If there's one thing New Yorkers know how to do, it's walk. But the lengthy tip-to-tip adventure is reserved for special occasions (like a milestone birthday à la Broad City, or in this case, a 75-degree day with zero humidity).
On this perfect NYC day, my fellow editor Ann Douglas Lott and I headed to the top of Manhattan to begin our adventure to the very bottom, which would conclude with 35K steps total, 16 miles, three bathroom stops, and a giant hot dog sighting.
We began at the Met Cloisters, as it's only a few blocks from the top, and you get a stunning view right off the bat. I must come clean that I did convince my boyfriend to drop us off at our starting point so we wouldn’t have to take the train from Brooklyn, but the A train and 1 train both run to the tippity top. For the Cloisters, hop off at Dyckman St. Now, let's begin our walk.
First leg: Hudson Heights and Riverside Park
Chamidae
The Met Cloisters to 84 St, 10:30am to 1pm
From the Cloisters, we walked the first 10 or so blocks through Hudson Heights and then veered off the main route to stroll through Riverside Park. Sticking to parks as much as possible while uptown is key, as you don’t have to wait for stoplights, and you avoid the city's congestion and are on to flatter terrain.
On this particular morning, the skies were so clear that you could see One World Trade in the distance, which is a lovely, albeit slightly scary, reminder that you have to go even further than that. Along the way, you’ll enjoy views of the George Washington Bridge, catch a glimpse of the Little Red Lighthouse, dodge bicycles, and, if you’re as lucky as us, watch a trombone player serenade the Hudson River and overhear kids in school yards enjoying field day. All the while, you might be wondering if those around you can tell you’re about to walk roughly 16 miles.
Around 100 blocks in, we took a slight detour inland to see Columbia University, which was ultimately a waste of steps as it was closed for Graduation. If you want to conserve your steps, keep heading south through the park instead. We returned to Riverside Park to continue along a calmer, less congested path. We didn't want to miss the 91st Flower Garden, famous for its cameo in the beloved NYC 1998 rom-com You’ve Got Mail. The garden was also the location of our first break and rehydration stop.
Once we had given our legs a little rest (we had already walked around 11K steps), we headed out of the park back on the main drag to snap a photo of the iconic Barney Greengrass before a truly mouthwatering lunch.
Second leg: lunch and Central Park
Ann Douglas
W 84th St to Lincoln Circle, 1pm to 3pm
Food is fuel, my friends, which is why we were already discussing lunch on the drive up to the Cloisters. We Brooklyn girls hardly frequent the Upper West Side, which is a shame because there are so many incredible places to eat up in this neighborhood. Example: Maison Pickle. It’s not far from the Museum of Natural History and equidistant from Riverside Park and Central Park, so even if you’re not walking the entire length of Manhattan, you could add each of these to a day-long itinerary.
This place is massive, so walking in for lunch on a Friday wasn’t a problem. We started with one of its “break breads,” a hot skillet of honey and butter-slathered pull-apart rolls that are the closest thing to donuts without having to pull out the fryer. For the main course, we each had a French dip sandwich – what Maison Pickle is best known for – with a side of pickles and a crisp Diet Coke.
We desperately needed an hour-long lunch, not only to refuel but also to rest our feet. By 2pm, we were back on Amsterdam Ave and en route to Central Park. This park is the place where I learned the magical art of wandering in New York. It's one of the best things to do in the city. You could spend days exploring Central Park, so if you feel pulled to venture along the twisting trails of the Ramble, stroll among the roses in the Conservatory Garden or just touch grass in Sheep Meadow, take a detour. Oh, and there are public bathrooms throughout the park (keep your standards low, though).
Tip: If you get too lost in the park, find a lamp post. The first two (or three if you’re far enough north) numbers show which cross street you’re at, and the last two numbers show which side of the park you’re on (odd numbers indicate the west side, and even numbers are for the east side). For example, the lamp post in the above photo reads 6319, meaning we were close to W 63rd St.
We entered the park at 81st St, across from the Museum of Natural History, and curved our way around the Lake, pausing to admire the boaters from the Bank Rock Bay bridge and the Ladies Pavillon before hitting Sheep Meadow. For the sake of time, we didn't venture east, but I would have loved to linger at Cherry Hill or beside the Pond. We exited in the southwestern corner of the park at Lincoln Circle.
Third leg: Times Square and Midtown
Chamidae
59th St to 23rd St, 3pm to 3:45pm
As we walked down Broadway, we knew one thing was coming – something most New Yorkers avoid with every chance they get. However, I am suggesting that hitting Times Square, for a moment at least, is bizarrely fun.
At this point in the journey, I can feel it. My hips and calves are starting to ache, the beauty of Central Park is long gone, and there is still much to go. Walking through Times Square and stumbling across a giant hot dog, a towering gorilla and a dance group all in one block of this overwhelming NYC landmark was hilarious. It felt chaotic, ridiculous and invigorating.
When Ann Douglas posted the above photo of me posing with the hot dog, a friend with a connection to the artists, Jen Catron and Paul Outlaw, swiped up and helped her get in touch with them to learn more about the hot dog's residency in Times Square, which will end June 13. Alongside the hot dog's daily confetti shower at noon, the artists have hosted events ranging from a "Hottest Dog" canine beauty pageant – a spin on the often problematic Miss America Pageants – to a Nathan's Hot Dog Eating Contest Qualifier, as well as talks on topics like hot dog street vendors' experiences and food justice.
"As we began to dig deeper, we have been just shocked at how much meaning we, and others, find in a hot dog. We have people proposing in front of the hot dog, people making pilgrimages to see it, dressed as hot dogs. It has been TikTok famous and also critically acclaimed. I feel like it offers Times Square both a fun, exciting moment. And, if viewers want to dig in, some deeper issues to unpack," Catron told Lonely Planet.
The magic of walking through Times Square! One minute, you're having a photoshoot in front of a giant hot dog, and the next, you're learning about sustainability in the meat industry from the artists behind the sculpture.
We broke out of that area at 47th St and headed to 6th Ave to walk a quieter route. We followed this until 34th St, where we ran back into Broadway, which we followed to Madison Square Park for a short rest and a regroup before beginning our hunt for an ice cream pick-me-up. On the way, we passed the NYC Portal next to the Flatiron Building – an installation that livestreams between NYC and Dublin. It was turned off at the moment, but we waved to our fellow editors in Dublin anyway.
Fourth leg: Caffè Panna and Lower Manhattan
Ann Douglas
E 19th St to Battery Park, 4pm to 5:45pm
I was determined to acquire a sweet treat on this journey. I’m determined to do this almost every day, but that’s beside the point. If you’re getting ice cream in Manhattan, it doesn’t get better than Caffè Panna. It’s on the most charming street – Irving Pl, right off E 19th St – and while you can usually spot the line for this place from Gramercy Park, it’s absolutely worth the wait. It changes its flavors daily, offering specialty sundaes, affogatos and soft serve with the option of adding a crunch and freshly whipped panna. We both went for a simple scoop of lemon olive oil ice cream. So refreshing.
Is it considered cheating if we stopped by our office for a bathroom break? It was technically on our route, and public bathrooms can be hard to come by when you’re out and about. Plus, hello, air conditioning break! We recharged and hit 5th Ave at around 4:30pm, walking a few more blocks to Washington Square Park. It was bustling with NYU grads in their caps and gowns on top of the typical sunny day crowd. We could have easily gone for a swim in the fountain in this perfect weather (please, don’t actually do that), and noticed one little boy splashing about (really, please don't).
The street names were no longer numbers. The end was near. With one hour left, we had a clear view of One World Trade. We ventured through SoHo (what I like to call “the mall”) and into Tribeca, where happy hour was in full swing, and al fresco diners were out on every block – the definition of summertime bliss in NYC.
We crossed into the Financial District, more commonly known as FiDi, passing the Oculus – probably the most bizarro-looking building in the city that doubles as a train hub and a mall. Right across the street is the September 11 Memorial Museum and its beautiful reflecting pools. It’s a nice place to sit if you need one more final break before reaching the bottom of Manhattan. We continued on, though, because we both had dinner plans and needed to squeeze in a shower before.
We rolled up to Battery Park, hips and calves in distress, to discover that a construction fence had been put up around the entire park, almost completely blocking the allegedly worth it view of the water and the Statue of Liberty. She barely peeked over the fence at us so we could get the validation we needed before parting ways.
Walk stats
- Steps: 35k+
- Miles: almost 16 with detours
- Total time (including stops): 7 hours and 15 minutes
- Bathroom stops: 3
- Elementary school field days witnessed: 3
- College graduations witnessed: 2
- Times we got catcalled: 5
- Giant hotdogs spotted: 1
The journey was certainly not about the destination on this beautiful Friday in May. If you decide to plan your own tippity top to tippity bottom journey, there are infinite ways to complete the quest. But as long as you’re in good company and bring your can-do New Yorker attitude, it will be the walk of a lifetime.
